Hate to admit it cause the theme is so cringey but 1951 Minstrel Man is a super fun game, drop targets (yes, drop targets !!) ball saver, just a fun game to play, but I would never own one, for obvious reasons.
I also love Williams Jungle,1960 cool backglass animation, fun shots, unique cabinet, just all around fun.
Oldest game I've played is wiffle, don't think there are any older than that.
B